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Melting point: 122-123 experimental product melting point: 120   mass of starting material: 1.04 mass of product: 0.85g    what is limiting reagent and percent yield?

Melting point: 122-123 experimental product melting point: 120   mass of starting material: 1.04 mass of product: 0.85g    what is limiting reagent and percent yield?

Macroscale and Microscale Organic Experiments
Macroscale and Microscale Organic Experiments
7th Edition
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Kenneth L. Williamson, Katherine M. Masters
Chapter8: Thin-layer Chromatography: Analyzing Analgesics And Isolating Lycopene From Tomato Paste
Section: Chapter Questions
Problem 10Q: A TLC plate showed two spots with Rf values of 0.25 and 0.26. The plate was removed from the...
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Melting point: 122-123

experimental product melting point: 120

 

mass of starting material: 1.04

mass of product: 0.85g 

 

what is limiting reagent and percent yield?

PROCEDURE: 1. To a 125 mL Erlenmeyer flask equipped with a magnetic stir bar and containing 20 mL of dichloromethane add 1 mL of benzaldehyde and 1.1 molar equivalence of benzyltriphenylphosphonium chloride (calculate amount). 2. Add 5 mL of freshly prepared 50% NaOH (2.5 g of NaOH in 5 mL H,0) and cover with a watch glass and stir the mixture for 30 min at room temp. 3. Transfer the mixture to a separatory funnel using dichloromethane (10 mL) and H,O (20 mL). Shake gently, allow the layers to separate, drain off the lower DCM layer into a beaker. Discard the aqueous (top) layer. 4. Spot a drop of this liquid onto a TLC plate (for later) and evaporate the combined organic layers on a hot plate (at 100 °C) to an oil (cease heating when bubbling ceases). 5. To the resulting clear oil add 10 mL 95% ethanol, mix and cool in an ice bath.
Transcribed Image Text:PROCEDURE: 1. To a 125 mL Erlenmeyer flask equipped with a magnetic stir bar and containing 20 mL of dichloromethane add 1 mL of benzaldehyde and 1.1 molar equivalence of benzyltriphenylphosphonium chloride (calculate amount). 2. Add 5 mL of freshly prepared 50% NaOH (2.5 g of NaOH in 5 mL H,0) and cover with a watch glass and stir the mixture for 30 min at room temp. 3. Transfer the mixture to a separatory funnel using dichloromethane (10 mL) and H,O (20 mL). Shake gently, allow the layers to separate, drain off the lower DCM layer into a beaker. Discard the aqueous (top) layer. 4. Spot a drop of this liquid onto a TLC plate (for later) and evaporate the combined organic layers on a hot plate (at 100 °C) to an oil (cease heating when bubbling ceases). 5. To the resulting clear oil add 10 mL 95% ethanol, mix and cool in an ice bath.
PROCEDURE: cont. 6. Collect the precipitate by vacuum filtration 7. Take a melting point, calculate a percent yield and obtain an IR spectrum. Note the absence of a carbonyl stretch peak at about 1700 cm'. 8. Take TLC of crude reaction product (Step 4) versus final product using hexane/ethyl acetate (95:5) as eluent. Include representation of developed TLC plate in lab notebook and report. Calculate all R,s. Comment on the relative spot intensities of the E and Z isomers present in the crude reaction product mixture.
Transcribed Image Text:PROCEDURE: cont. 6. Collect the precipitate by vacuum filtration 7. Take a melting point, calculate a percent yield and obtain an IR spectrum. Note the absence of a carbonyl stretch peak at about 1700 cm'. 8. Take TLC of crude reaction product (Step 4) versus final product using hexane/ethyl acetate (95:5) as eluent. Include representation of developed TLC plate in lab notebook and report. Calculate all R,s. Comment on the relative spot intensities of the E and Z isomers present in the crude reaction product mixture.
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